Fashion

6 ways to wear loafers with socks and midi skirts in autumn/winter 2025

Street style experts prove the versatility of this winning combination.
6 Ways To Wear Loafers With Socks And Midi Skirts In AutumnWinter 2025
Jeremy Moeller/Getty Images

Fashion recently has been defined by shoes. They're the way to make a bold statement: from the popularity of furry styles sweeping through every brand from Dries Van Noten to Erdem, to Margiela Tabis taking over the mainstream. At the moment, however, we've decided to go back to basics, following the classic fashion lessons of Miu Miu and Givenchy.

The best loafers stood out on the runway not only for their timelessness, but also for their versatility. Ranging from chunky soles to flat, they often come in neutral colours like brown and black, but also often dabble in red, oxblood and burgundy.

Street style experts, always on the lookout for autumn/winter 2025 shoe trends, have wasted no time in establishing loafers as a piece that can be just as interesting as furry footwear. Worn with socks and midi skirts, they give off that preppy chic energy that works just as well for the office as it does for a day out.

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Here are our tips for wearing loafers with socks and midi skirts this autumn/winter 2025

Opt for comfortable garments such as sweaters
Katie Holmes con mocasines calcetas falda midi y suter en Nueva York.
Katie Holmes con mocasines, calcetas, falda midi y suéter.Michael Simon / Getty Images.

In recent years, Katie Holmes has become a great reference for dressing comfortably with pieces that don't shout, but command attention nevertheless. One of her tricks is to wear socks with patent loafers, giving that academic look but with a fun twist. The result is a casually distinguished aesthetic, with a camel sweater and black midi skirt.

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A solid, neutral colour palette never goes wrong
Mocasines con calcetas falda midi y blusa sin mangas en el street style.
Mocasines con calcetas, falda midi y blusa sin mangas.Valentina Valdinoci / Launchmetrics / Spotlight.

Employing neutral colours is a no-brainer for easy dressing, whether you're a lover of minimalism or just want to look good without too much effort. While wearing all black will never go out of style completely, this year, chocolate brown has taken centre stage as the star neutral shade. Go for a midi skirt and blouse in similar shades, perhaps opting for a striped or checked pattern if you want some fun! Black almond-toe loafers, long white socks and a blazer will top off this easy but effective look.

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Don't be afraid of dramatic garments like midi balloon skirts
Mocasines con calcetas falda midi y chaqueta de manga corta en el street style.
Mocasines con calcetas, falda midi y chaqueta de manga corta.305pics / Getty Images.

T-shirts are not only a closet staple, they can also be a very helpful grounding element when pairing them with more dramatic items like midi balloon skirts. Ballooning bottoms have been a stand-out trend this year, from trousers like bloomers and salwar-inspired pants, to bubble mini skirts. As the weather gets colder, you can opt for their longer cousin, the midi balloon skirt. A simple t-shirt avoids overloading the look, and gives you room to play with a matching jacket. Simple black loafers and perhaps some fun statement socks are the way to finish the look off.

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Adapt loafers to any wardrobe with socks and midi skirts
Mocasines con calcetas y falda midi color beige y camisa negra en el street style.
Mocasines con calcetas y falda midi color beige y camisa negra.Christian Vierig / Getty Images.

Loafers and socks are a duo that brings to mind the preppy, nerdy chic aesthetic that has become so popular with Gen Z, thanks in no small part to Miu Miu. However, that's not to say that more advanced fashion-lovers can't explore this combo. In fact, loafers and socks would fit into a mature wardrobe perfectly: classic style staples like pleated midi skirts, polo shirts and black shirts would look perfect.

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Choose garments with details that are hard to ignore
Mocasines con calcetas falda midi y suter de cuello alto en el street style.
Mocasines con calcetas, falda midi y suéter de cuello alto.Jeremy Moeller / Getty Images.

If you're going for simplicity on the bottom, perhaps opt for something a little more interesting on top. Turtleneck sweaters are a signature piece for the colder months due to their practicality, but recently they've been remixed to add some drama: sequins, puffed sleeves, structured shoulders… These details instantly bring some excitement to the look and can be worn with something as casual as jeans. But, if you're going for a slightly more elegant look, choose a straight midi skirt, flat loafers and neutral socks.

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Combine different aesthetics in one look
Mocasines con calcetas falda midi de encaje y camisa de mezclilla en el street style.
Mocasines con calcetas, falda midi de encaje y camisa de mezclilla.Francesca Babbi / Launchmetrics / Spotlight.

Employing contrasting styles has been a defining concept over the past few seasons. For example, hybrid shoes like sneakerinas have been ever-present in major fashion capitals. A simple way to create a look that juxtaposes aesthetics would be to mix romantic and utilitarian garments. Take notes from the above shot: a sheer, lacy dress, loafers with socks and an oversized denim shirt to toughen it all up.

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A version of this article was originally published on Vogue Mexico and Latin America.

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